Stereochemical requirements of chitin synthase for ligand binding at the allosteric site for N-acetylglucosamine

European Journal of Biochemistry

Volumn 237, Issue 2, 1996, Pages 476-482

  Horsch, Markus ^a   Mayer, Christoph ^a   Rast, Dora M ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

Author keywords

Allosteric activation; Chitin synthase; Kinetics; N acetylglucosamine; N acetylglucosaminono 1,5 lactone oximes

Indexed keywords

CHITIN SYNTHASE; GLUCOSAMINE DERIVATIVE; N ACETYLGLUCOSAMINE; N ACETYLGLUCOSAMINE 1,5 LACTONE OXIME; UNCLASSIFIED DRUG;

AMPEROMETRY; ARTICLE; BINDING SITE; CONTROLLED STUDY; ENZYME BINDING; ENZYME ISOLATION; ENZYME KINETICS; ENZYME STRUCTURE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; LIGAND BINDING; MUCOR; NONHUMAN; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 0029865247     PISSN: 00142956     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1432-1033.1996.0476k.x     Document Type: Article

References (35)

1. de Rousset-Hall, A. & Gooday, G. W. (1975) A kinetic study of a solubilized chitin synthetase preparation from Coprinus cinereus, J. Gen. Microbiol. 89, 146-154.
2. Hänseler, E., Nyhlén, L. E. & Rast, D. M. (1983) Dissociation and reconstitution of chitosomes, Biochim. Biophys. Acta 745, 121-133.
3. Glaser, L. & Brown, D. H. (1957) The synthesis of chitin in cell-free extracts of Neurospora crassa, J. Biol. Chem. 228, 729-742.
4. Porter, C. A. & Jaworski, E. G. (1966) The synthesis of chitin by particulate preparations of Allomyces macrogynus, Biochemistry 5, 1149-1154.
5. McMurrough, I. & Bartnicki-Garcia, S. (1971) Properties of a particulate chitin synthetase from Mucor rouxii, J. Biol. Chem. 246, 4008-4016.
6. Gooday, G. W. & de Rousset-Hall, A. (1975) Properties of chitin synthetase from Coprinus cinereus, J. Gen. Microbiol. 89, 137-145.
7. Furter, R. (1985) Die Chitinsynthese des dimorphen Zygomyceten Mucor rouxii, Ph.D. thesis, University of Zürich.
8. Ricard, J. & Cornish-Bowden, A. (1987) Co-operative and allosteric enzymes: 20 years on, Eur. J. Biochem. 166, 255-272.
9. Kang, M. S., Elango, N., Mattia, E., Au-Young, J., Robbins, P. W. & Cabib, H. (1984) Isolation of chitin synthetase from Saccharomyces cerevisiae, J. Biol. Chem. 259, 14966-14972.
10. Ruiz-Herrera, J., Lopez-Romero, E. & Bartnicki-Garcia, S. (1977) Properties of chitin synthetase in isolated chitosomes from yeast cells of Mucor rouxii, J. Biol. Chem. 252, 3338-3343.
11. Cabib, E. (1987) The synthesis and degradation of chitin, Adv. Enzymol. 59, 59-101.
12. Rodewald, R. (1990) 16 S-Chitinsynthetase aus Agaricus bisporus. Reinigung und Hemmbarkeit durch antifungale Agenzien, Ph.D. thesis, University of Zürich.
13. Lending, C. R., Leal-Morales, C. A., Flores-Martinez, A., Bracker, C. E. & Bartnicki-Garcia, S. (1991) Purification and characterization of 16 S chitin synthetase particles from cell walls of Mucor rouxii, Exp. Mycol. 15, 11-25.
14. Beer, D. & Vasella, A. (1985) Aldonhydroximo-lactones. Preparation and determination of configuration, Helv. Chim. Acta 68, 2254-2274.
15. Beer, D., Maloisel, J.-L., Rast, D. M. & Vasella, A. (1990) Synthesis of 2-acetamido-2-deoxy-D-gluconhydroximolactone- and chitobionhydroximolactone-derived N-phenylcarbamates, potential inhibitors of β-N-acetylglucosaminidase, Helv. Chim. Acta 73, 1918-1922.
16. Rast, D. M., Horsch, M., Furter, R. & Gooday, G. W. (1991) A complex chitinolytic system in exponentially growing mycelium of Mucor rouxii: properties and function, J. Gen. Microbiol. 137, 2797-2810.
17. Bartnicki-Garcia, S., Bracker, C. E., Reyes, E. & Ruiz-Herrera, J. (1978) Isolation of chitosomes from taxonomically diverse fungi and synthesis of chitin microfibrils in vitro, Exp. Mycol. 2, 173-192.
18. Monod, J., Wyman, J. & Changeux, J.-P. (1965) On the nature of allosteric transitions: a plausible model, J. Mol. Biol. 12, 88-118.
19. Pravdiç, N. & Fletcher, H. G. (1971) The oxidation of partially substituted 2-acetamido-2-deoxy-aldoses with methyl sulfoxide/acetic anhydride. Some 2-acetamido-2-deoxyaldonic acid derivatives, Carbohydr. Res. 19, 353-363.
20. Horsch, M. & Rast, D. M. (1993) Allosteric activation of chitin synthetase by N-acetylglucosamine: a mechanistic study, in Chitin enzymology (Muzzarelli, R. A. A., ed.) pp. 47-56, Eur. Chitin Soc., Ancona.
21. Hervé, G. (1989) Aspartate transcarbamylase from Escherichia coli, in Allosteric enzymes (Hervé, G., ed.) pp. 61-80, CRC Press, Boca Raton.
22. Horsch, M., Hoesch, L., Fleet, G. W. J. & Rast, D. M. (1993) Inhibition of β-N-acetylglucosaminidase by glycon-related analogues of the substrate, J. Enzyme Inhib. 7, 47-55.
23. Horsch, M., Hoesch, L., Vasella, A. & Rast, D. M. (1991) N-Acetyl-D-glucosaminono-1,5-lactone oxime and the corresponding (phenylcarbamoyl)oxime. Novel and potent inhibitors of β-N-acetylglucosaminidase, Eur. J. Biochem. 197, 815-818.
24. Legler, G. (1990) Glycoside hydrolases: mechanistic information from studies with reversible and irreversible inhibitors, Adv. Carbohydr. Biochem. 48, 319-384.
25. Horsch, M. (1991) N-Acetylglucosaminonoxime als Modulatoren von Chitinsynthetase und von chitinolytischen Enzymen, Ph.D. thesis, University of Zürich.
26. Cubero, B., Ruiz-Herrera, J. & Cerda-Olmedo, E. (1993) Chitin synthetase mutants of Phycomyces blakesleeanus, Mol. & Gen. Genet. 240, 9-16.
27. Furter, R. & Rast, D. M. (1985) A comparison of the chitin synthase inhibitory and antifungal efficacy of nucleoside-peptide antibiotics: structure-activity relationships, FEMS Microbiol. Lett. 28, 205-211.
28. Wessels, J. G. H. (1993) Wall growth, protein secretion and morphogenesis in fungi, New Phytol. 123, 397-413.
29. Leal-Morales, C. A., Bracker, C. E. & Bartnicki-Garcia, S. (1988) Localization of chitin synthetase in cell-free homogenates of Saccharomyces cerevisiae: chitosomes and plasma membrane, Proc. Natl Acad. Sci. USA 85, 8516-8520.
30. Bartnicki-Garcia, S. (1989) The biochemical cytology of chitin and chitosan synthesis in fungi, in Chitin and chitosan (Skjak-Braek, G., Anthonsen, T. & Sandford, P., eds) pp. 23-35, Elsevier Science, London.
31. Balch, W. E. (1989) Biochemistry of interorganelle transport. A new frontier emerges from versatile in vitro model systems, J. Biol. Chem. 264, 16965-16968.
32. Martinez, J. P., Gimenez, G. & Bartnicki-Garcia, S. (1987) Intracellular localization of UDP-N-acetylglucosamine in Neurospora crassa wild-type and slime mutant strains, Exp. Mycol. 11, 278-286.
33. Perez, M. & Hirschberg, C. B. (1985) Translocation of UDP-N-acetylglucosamine into vesicles derived from rat liver rough endoplasmic reticulum and Golgi apparatus, J. Biol. Chem. 260, 4671-4678.
34. Gooday, G. W., Zhu, W.-Y. & Donnell, R. W. (1992) What are the roles of chitinases in the growing fungus, FEMS Microbiol Lett. 100, 387-391.
35. Mayer, C., Horsch, M., Linder, C. & Rast, D. M. (1993) Purification and substrate specificity of a β-N-acetylglucosaminidase from growing hyphae, in Chitin enzymology (Muzzarelli, R. A. A., ed.) pp. 485-492, Eur. Chitin Soc., Ancona.